


Fake Dating

by imagineteamfreewill



Series: 25 Days of Tropes [4]
Category: Supernatural
Genre: Christmas, Christmas Fluff, Christmas Party, Co-workers, F/M, Fake/Pretend Relationship, basically a hallmark movie
Language: English
Status: Completed
Published: 2020-01-07
Updated: 2020-01-07
Packaged: 2021-02-26 05:31:16
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,699
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22153537
Author URL: https://archiveofourown.org/users/imagineteamfreewill/pseuds/imagineteamfreewill
Summary: Based off the prompt "fake dating".
Relationships: Dean Winchester & You, Dean Winchester/You, reader x dean - Relationship
Series: 25 Days of Tropes [4]
Series URL: https://archiveofourown.org/series/1594564
Kudos: 42





	Fake Dating

**Author's Note:**

> This series is technically supposed to be short fics, but this one ended up being regular one shot length! Enjoy!
> 
> This fic was originally posted on my tumblr of the same name on December 29th, 2019.

The prospect of having to go alone to Christmas breakfast at your aunt’s house was becoming more and more daunting as the day neared. This would be the tenth Christmas since going away to college that you’d come home alone, and your aunts and cousins wouldn’t let you live it down. Coming home for a few years without a man by your side wasn’t bad, but ten years? Unheard of in your family. All the other cousins were either engaged or married already. So when your phone lit up with your aunt’s name, breaking your concentration and distracting you from your work, you knew that you had to do something. Posting an ad online for a fake boyfriend wasn’t an option, but the more you thought about it, the more you realized you didn’t have any other option.

_My life is turning into a frigging Hallmark movie,_ you thought, groaning quietly.

Sighing, you stood up from your desk and stretched before heading around the corner towards the bathroom.

“Y/N! Y/N, hey!”

You stopped, turning around and grinning when you saw Dean standing up in his own cubicle, grinning back at you.

“What?” you asked.

“You’re coming to Game Night tomorrow, right? I’m sick of losing, so we need to beat Charlie and Sam,” Dean said. His shirt sleeves were rolled up, the fabric tight against his muscles as he crossed his arms and leaned against the dividers. You had to admit that his physique was distracting, but only a little bit. A little bit was all you allowed yourself.

You groaned. “I forgot Game Night was tomorrow! I have to get to the airport—I’m flying out to Ohio right after work.”

“But it’s Christmas Eve, Y/N! You’re telling me you’d rather go to Ohio than spend time with your friends?”

“I wish I could stay, but I—” You stopped as a plan started to form in the back of your mind. “Hey, you still owe me that favor. That _big_ favor.”

Dean watched you warily, clearly confused about the sudden change in subject. “Yeah… I mean, I didn’t think it was _that_ big of a favor to watch Sam after his surgery— Okay, fine, it was a big favor,” Dean relented, seeing the annoyed look on your face.

“I’m cashing in,” you told him. After a quick glance around the office to make sure there were no obvious eavesdroppers, you continued, “I’ll take care of everything, but I need you to pretend to be my boyfriend for Christmas.”

“What? Y/N, stop mumbling.”

“I need you to be my boyfriend for Christmas,” you mumbled again, slightly louder this time.

“What are you saying?”

“I need you to be my boyfriend for Christmas, okay?”

The words came out as a half-shout and one of your co-workers from down the row stood up, surprised at the outburst. You felt your cheeks go hot and you hid your face with one hand, avoiding eye contact with Dean.

Grabbing your elbow, Dean pulled you away from his cubicle and led you down the aisle to the empty copy room. You stepped away from him as soon as he dropped your arm.

“Y/N, what the hell are you talking about?” Dean asked. “You want me to pretend to be your boyfriend? Like a chick flick or something?”

You wiped your palms on your slacks, nervous. “Yeah. My aunt has this big Christmas breakfast thing and I— I go alone every year. It’s hell with all my cousins either married or engaged now, and I don’t think I can stand another year of the questions and the teasing and the torture. I just need you to pretend to be my boyfriend for three days, and then you’re off the hook. I know it’s a lot to ask, but I’ll pay for your airfare and a room of your own and all your food.” You stopped rambling and took a breath, watching Dean as he processed your request.

Finally, he nodded. “Okay. I owe you one, and after all the other things you’ve done for me that I’ve never paid you back for… This sounds like a fair deal.”

Relief flooded you and you felt the tension in your shoulders melt away. “Really?” you asked, and he nodded again. “Thank you, Dean. Really.”

He shrugged. “It’s no problem, Y/N. Just, uh, text me some of the details. You know, things I should know for the breakfast and stuff.”

You nodded, watching him as he rubbed the back of his neck, then turned and walked back to his cubicle. Closing your eyes, you leaned against the wall and tried to collect yourself.

_I can’t believe I just did that._

* * *

Dean walked with you to the parking garage the next afternoon. He was quiet as you pulled your suitcase from your car to his, handing it off to him before climbing into the passenger seat of his Impala. 

“You don’t have to do this,” you said as he got in on his own side. “You can change your mind.”

He shook his head, glancing over at you. “I gave you my word that I would, Y/N. Besides, I’m not about to turn down a free trip. Sam’s gonna be with Jess and Charlie’s gonna be with her girlfriend… This’ll be good. My only regret is agreeing to flying… I’m not really a big fan of planes.”

“Me neither,” you agreed. “But it’s faster than driving, and I try not to draw this kinda thing out.”

“I don’t blame you,” Dean said. He pulled his car out of its spot and headed out of the garage, and soon you were on your way to the airport.

The airport wasn’t far from your office building. Dean parked in the garage and helped you with your luggage like a perfect gentleman, and you smiled as you took it from him.

“You don’t have to act like my boyfriend now, Dean. We’re not there yet,” you told him. “You can tease me like you normally would and let me get my own stuff out of the back.”

He shrugged a little and closed the trunk with his free hand. “Consider it practice.”

Not wanting to argue, you followed him inside and through security. The lines were long, and by the time the two of you reached your gate, your flight was already boarding. Thankfully, there were two seats next to each other near the front of the plane. Dean sat down and immediately closed his eyes, clearly anxious.

“Hey,” you said as the flight attendants moved past you to check for seatbelts. Dean glanced over at you, his hands gripping the armrests. Hesitantly, you placed your hand over his. “We’re gonna be fine. It’s a short flight—only two hours.” When he didn’t respond, you continued, “I downloaded one of the newer Star Wars movies on my phone. Watch it with me?”

After a second, Dean let out a slow exhale and nodded tightly. He opened his eyes, giving you a tense smile when you held out an earbud for him. It was accepted without comment, but you felt Dean slowly start to relax beside you as the flight attendants went through their regular safety speeches. When the plane began take-off, he tensed again. You remained silent, letting him do what he needed to, until finally the aircraft leveled out and he focused on the movie once more. Turbulence was minimal the entire flight, and your movie was almost over as the plane landed in Cleveland. 

“You doing okay?” you asked as you and Dean headed through the terminal to the rental car office. 

“I’m fine, babe,” he answered, wrapping an arm around your waist. You tensed, stopping for a moment before forcing yourself to relax and walk with him.

“This is going to take some getting used to,” you laughed, and Dean laughed along with you.

Two hours later, you and Dean pulled up outside your hotel, both of you equally exhausted. The rooms were ready for you, thankfully, and as soon as you were unpacked enough to get ready in the morning without any issues, you knocked on the door separating your room from Dean’s.

“It’s unlocked,” Dean called to you. 

You pushed the door open, standing in the doorway as Dean continued to unpack his things. “So… What’s the plan? Did you read that text I sent you?”

Dean nodded, only glancing up at you for a second before gathering up some shirts and carrying them to the closet. He began to hang them up with his back to you as he replied, “Yeah. I got the whole run-down on the family, and I checked out your Facebook pics to put faces with names.”

“You have a Facebook?”

“I made one last night,” he said. Dean turned and looked at you. “I sent you a friend request, I think. I’m still figuring it out, Sam wasn’t around to help.”

_Dean made a Facebook for this?_

You stared at him for a second, dumbstruck. “Right. Um, well, we should figure out some sort of story.”

Shrugging, Dean stuck his hands in his pockets and leaned against the dresser with the TV. “Easy. We’ve been friends for a long enough time that we know a lot about each other already, so we can just say that we met at work. I thought you were cute and invited you to Game Night and the rest is history.”

“Well… I guess that’s not too far off from the truth,” you answered. “I made a list of things that you should probably know. You know, things that I don’t normally tell people I’m not super close with.”

You dug the list out of your pocket and held it out for him. Dean took it in silenced, unfolding the paper and looking it over for a minute before nodding and slipping it into his back pocket. 

“I’ll make a list or something, too. Can I just text it to you?”

You nodded, suddenly uncomfortable as you thought of the next thing on your mental to-do list. You knew that this would be weird, but you’d been hoping it wouldn’t be this weird.

“We should talk about some other things too, Dean. Like kissing and stuff.”

“And stuff?” Dean asked, raising his eyebrows.

Your face felt warm. “Yeah, and stuff. What exactly are you comfortable with?” He shrugged again and you sighed. “Okay, how long have we been dating, according to your story?”

“About four months,” Dean replied after a moment. 

“Okay… So we’ve probably only kissed, then.”

Dean’s eyebrows shot up again. “Whoa, wait. Four months is a long time, Y/N. You’re saying that we’ve only kissed? Isn’t that a little… I don’t know… middle school?”

“I dated my last boyfriend for over a year and we hadn’t done anything other than kissing a little… touching,” you told him.

You wanted to crawl into a hole and die. Talking about your last relationship with Dean was weird enough, but talking about how physical you’d gotten—and not gotten? Mortifying.

After a long moment, Dean finally nodded. “Alright. Just kissing, then.”

Dean’s phone chirped on the nightstand and you looked over at it. “Okay. I should probably head to bed, then,” you said, looking back at him. “We should probably leave around seven to get to my aunt’s house.”

“Okay. See you in the morning, sweetheart. Sleep tight.”

You gave Dean an awkward smile before backing into your room and shutting the door, locking it on your side. Your stomach gurgled and you sighed, knowing that you wouldn’t be getting any sleep tonight. Anxiety would most certainly keep you awake and as you went through your nightly routine, you tried not to think about what the next morning would hold for you. Nonetheless, the thoughts filled your head and you crawled into bed fully aware that you wouldn’t sleep a wink.

_______________

“Aunt Cindy, it’s so good to see you!”

Your aunt pulled you into a tight hug, leaving you breathless and already overwhelmed by the time she let go. Quickly, before she could grab you again, you stepped out of the way to reveal Dean standing in the doorway.

“Aunt Cindy,” you began with a smile, “This is Dean, my boyfriend. I hope you don’t mind that I brought him…”

She smiled wider, shaking her head and pulling Dean in for a hug. He grunted and you held back a laugh as you shucked off your shoes and coat.

“Not at all, dear! It’s so wonderful of you to finally have someone to bring along!”

“That’s one way of putting it,” you mumbled as she released Dean. Almost immediately, he stepped out of arm’s reach and began removing his coat and shoes as well.

“Thanks for having me,” Dean said, smiling politely. “I know it’s last minute, but when I found out that there’d be cinnamon rolls…” He trailed off and you knew by the way your aunt’s eyes lit up that she’d taken the bait.

“Oh yes, my cinnamon rolls!” she cried. “They’ve won awards all over the county. Come along, Dean, I’ll serve you one while you tell me all about yourself.”

Before he could get out any kind of response, Dean was being dragged to the kitchen, leaving you alone. You grinned at the pleading, helpless look he gave you on his way out.

“Guess it’s just you and me, Rocky,” you sighed, crouching down to pet the old basset hound who’d come to greet you. He was normally your only companion during Christmas and as much as you loved him, you were relieved that Dean would be accompanying you this time.

Rocky barked, accepting your gentle pets before heading off to find a new person to occupy him. You stood and followed Dean’s path into the kitchen, smiling tightly when your cousin Jane made eye contact with you from her spot by the sink. She set down her drink—a mimosa with more champagne than juice, probably—and made her way towards you, grabbing her fiance on the way.

“Y/N! It’s so good to see you!” she cheered, and you let her pull you into a hug.

“So you good to see you, too,” you replied. “I didn’t think you’d be so excited to see me, considering I couldn’t come to your bridal shower…”

_More like wouldn’t come,_ you thought.

Jane laughed, throwing her head back in a way that looked like it hurt. Her fiance smiled politely, his hand on the small of her back. “Don’t be silly, Y/N! Of course I want to see my littlest cousin! Besides, I need to hear about all the cute boys at your new office. Surely you’ve had the chance to go out with all of them by now?”

She raised an eyebrow at you and you felt sick to your stomach. _Of course. What would Christmas be if Jane wasn’t torturing me about how she always got more dates than me?_

“Actually—”

“Hi, you must be Jane.” Dean’s voice and his hand on the small of your back almost made you jump, but you were immediately filled with relief that he’d found you. He held out a hand, shaking with Jane and her fiance, and when you glanced back at him, he smiled charmingly. So charmingly, in fact, that your heart skipped a beat.

“Indeed I am. Who are you?” Jane replied, raising an appreciative eyebrow as she looked Dean over from head to toe.

You held back a disgusted scoff. Surely her fiance was seeing this. _Does he know she’s been cheating on him from the start?_

“I’m Dean, Y/N’s boyfriend. It’s nice to finally meet you, she talks so much about her family. I didn’t know you were engaged—when she showed me your Instagram, it looked like you weren’t even in a relationship.”

Jane’s face transformed into one of horrified shock as her fiance slid his arm around her waist, his eyes cloudy with anger.

“Would you excuse us?” he asked.

Dean nodded, trying to hide a smile as the two of you watched Jane and her fiance walk away, whispering fiercely as they headed to the empty side of the house.

“Dean, oh my God,” you laughed, looking up at him. “That was insane, how did you know that she was cheating on him? I’ve never been able to find her on Instagram, her account’s super secretive!”

Shrugging, Dean dropped his hand from your back. “I have my ways. Did you wanna eat? I can distract your family while you get some food.”

You shook your head, giving him a grateful smile. “I had something back at the hotel, but thanks. For all of this, really.”

Dean opened his mouth to say something, only to be cut off by your aunt yelling your name. You winced and Dean raised an eyebrow.

“You wanna get out of that?” he asked, his voice low. You nodded. “You trust me then, right?” 

You nodded again and Dean took your hand, leading you in the direction that Jane and her fiance had left. You followed him blindly, grinning a little when you saw the dumbfounded looks your other cousins were giving you as Dean led you out of the kitchen. They were blatantly ogling him, but you couldn’t blame them. The red shirt and dark jeans he was wearing made you want to ogle him too, and you _definitely_ had that morning at the hotel. He’d been getting coffee while you waited for him at the tables in the lobby and _man,_ what a view you’d had. Your face went red at the thought and you couldn’t wipe the giddy smile off your face as Dean slowed.

He led you into your uncle’s empty office, closing the doors behind you.

“What are we doing here?” you asked, looking around. It had been ages since you’d spent time with your uncle, but you had fond memories of reading and sketching by the big windows along one office wall.

“Nothing. Talking. Whatever you want to do,” Dean answered. He perched himself on the long edge of the desk, watching as you walked along the built-in shelves, trailing your fingers across the spines of the books.

“I haven’t been in here in forever,” you murmured. “I spent so much time here as a kid.”

“Yeah?”

You nodded, glancing over at Dean before returning to the books. “Yeah. My uncle and I were close when I was little, but not so much anymore. I realized as I got older that I didn’t really agree with him on a lot of important things, and it kinda created a rift between us.”

“That must be hard.”

Shrugging, you stopped and looked over at Dean. Down the hall, you heard someone say your name, then knock on another door. Your eyes grew wide, but Dean only grinned and gestured for you to come closer.

“What are we gonna do? My aunt doesn’t like people snooping around—she’s always been possessive of her stuff,” you hissed.

Dean shook his head, spreading his legs slightly and gesturing for you to stand in between them. You did as he instructed, feeling heat spread to your cheeks as you realized just how close you were.

“Can I kiss you?” Dean whispered.

“Dean, now’s not the—” You stopped, realizing his intentions. Slowly, you nodded.

Smiling softly, Dean reached up and cupped your cheek with his hand, gently pulling you closer. “Relax,” he murmured, and then his lips were on yours.

It took you a second, but you found yourself relaxing and leaning into the kiss as if you’d kissed Dean a thousand times before. Your hands went immediately to his red overshirt, clutching the edges of the soft fabrice as his other hand wound around your waist and pulled you closer. You moaned against his lips, deepening the kiss and letting him slide his hand up into your hair as the office doors opened behind you.

“Y/N!” your aunt gasped.

You pulled away, your eyes searching Dean’s for a moment before you turned and looked over your shoulder at your aunt, who looked positively scandalized. Your brain was still processing the kiss—_the very good kiss,_ it helpfully reminded you—but thankfully, Dean’s processing time was shorter than yours. He slid his hand into yours and stood, forcing you to step away from him.

“We’re so sorry,” he apologized, but you could hear the smile in his voice. “We got a little caught up. Y/N was telling me about how much she used to love this room as a kid, and then I wanted to see it, and we—” Dean gestured with his free hand and the shocked expression on your aunt’s face lessened slightly.

“Yes, she and Tom always did get along. I’m glad that you have such fond memories here,” your aunt replied, casting a glance your way. You smiled nervously and tried not to think about how sweaty your palm was against Dean’s, or how his lips had felt so good against yours.

“Well,” Aunt Cindy continued, clapping her hands together, “if you two are… done… We’re serving up more drinks in the dining room. There’s coffee, if you want it.”

“We love coffee,” Dean answered. He squeezed your hand as your aunt left, then looked back at you. “You okay?”

Swallowing hard, you nodded and tried not to look as dumbstruck as you felt. “Me? Oh yeah. I’m great. Never better.”

Dean chuckled and tugged on your hand till you walked with him. “I could get used to this,” he said.

“Used to what?” you asked.

“This. Us. You.” He lifted your joined hands for emphasis. “I’d be lying if I said I hadn’t thought about it before.”

“About what? Dating me?” 

“You say that like it’s surprising,” Dean replied. He stepped out of the way of some children running past, pulling you up against him so you were out of the way. Your breath caught in your throat when you felt the way his arms wrapped around you so easily, like he’d been holding you for years now.

“It’s—” You stopped and shook your head, stepping away from Dean when the coast was clear.

“It’s what, Y/N?”

You shrugged. “I don’t know. I just figured you’d go for someone more like the girls who work in PR,” you said after a second.

The corners of Dean’s lips turned down slightly. “Why wouldn’t I go for you? You’re the most beautiful girl on the whole floor, and I knew from the second you helped me beat Sam you first game night that I wanted you.”

“Really?” you laughed. “Dean, that was like, two years ago.”

“I know. We were playing Clue and you were one of the most competitive people I’d ever met. You still are.”

You couldn’t help but smile at that. “I can’t believe you still remember that. Besides, I’m pretty sure we only won because you told Sam and Charlie to go easy on “the cute girl from work”… Yeah, don’t think I didn’t hear that little conversation when I got up to go to the bathroom”

Dean rubbed the back of his neck, his ears turning red when he realized you’d caught him. “That’s what you remember?” he asked.

Still smiling, you took his hand and laced your fingers together, leading him the rest of the way to the dining room. Your aunt had set out mugs and glasses across the table and you laughed a little when Dean made a beeline for the coffee.

“He’s a nice guy.” You jumped in surprise, turning around to find Aunt Cindy standing close by. “He hasn’t tried to hit on any of your cousins yet.”

“Yet?” you asked, crossing your arms over your chest.

“It was a compliment, Y/N, don’t be so—”

“It wasn’t a compliment and we both know it,” you huffed, not wanting to hear whatever else she had to say. “Thanks for inviting me, Aunt Cindy, but I think Dean and I are gonna head out.”

“So soon?” she asked.

You gave her a tight smile. “We have other plans today. Dean!” You turned on your heel, heading towards your “boyfriend”.

“Everything okay?” he asked, seeing the frustration on your face when you got closer. He was holding your uncle’s old coffee mug and you took it from him, setting it on the table.

“We’re leaving. We have to get to your brother’s party, remember?”

Dean nodded, immediately recognizing the phrase from your conversation earlier. He’d agreed to leave, no questions asked, should you mention going to Sam’s party, and in this moment, you were more than thankful. No one had to know that Sam was currently a two hour flight away.

“Right, I forgot,” he said. Dean smiled politely at the man he’d been starting to talk with, then let you lead him out of the dining room and to the door.

Your aunt was waiting with your coats. “I’m so sorry you have to leave so early!” she cried. You could tell she was putting on the works for Dean’s sake, and you realized after glancing at him that he could tell too.

“I don’t think my mom would be too happy if she didn’t get to meet Y/N before lunch,” Dean said good-naturedly. “Thanks for having us.”

“Anytime, sweetheart. And if you wanna come over without Y/N, we’d love to have just you. It would be nice to get to know you more…” You held back a gag when she laid her hand on Dean’s arm.

“Thanks, but no thanks,” Dean replied, and your heart stopped in your chest. Your aunt was staring at him, clearly about to comment on his rude answer, but he continued, “You treat Y/N like she’s dirt, but she’s worthy of more than I can give her. I’m lucky to have her, and you’re lucky that there’s some so amazing in your life. Y/N works hard at her job, loves her friends more than anything, and values family so much that she comes to your breakfast every year, regardless of how much you torture her or put her down.”

Your aunt stared at Dean, speechless, as did you. After a second, he slipped on his coat and took your hand. “You ready?” he asked.

Nodding dumbly, you let Dean pull you behind him until the two of you were back in the rental car.

“Dean—”

“Before you say I shouldn’t have done that, let me say something—”

“That’s not what I was gonna say,” you interrupted, smiling a little. “I was just gonna say thank you.”

Dean nodded, his hands on the steering wheel. “You deserve it. Someone’s gotta tell them how great you are, since they clearly don’t see what I see.”

You ducked your head, your cheeks warm. “Dean… After this…”

“If you just wanna go back to being friends, we can make it work, Y/N. Game Night’s always been open to you and it always will be,” Dean said.

“And what if I don’t wanna go back to being friends?” you asked, risking a glance at him. He was smiling, and the butterflies in your stomach fluttered at his boyish grin.

“Well, then I guess we’ll have some ‘splainin to do.”

You laughed, shaking your head at him as he started the car and pulled out of the driveway. “Dean Winchester, did you just quote_ I Love Lucy?”_

“Maybe, but if you try and tell anybody, I’ll deny it.”

Grinning, you sat back in the seat and watched as Dean drove back to the hotel. When you passed a movie theater, you sat up and pointed out the window.

“Wait, Dean! Let’s go see a movie!” you cried.

“On Christmas?” he asked, glancing over at you before merging into the turn lane.

“It’ll be emptier than normal, and we can see that new movie you’ve been wanting to see…”

Dean’s grin matched yours as he pulled into the parking lot and parked the car. “Deal. I’ll get the tickets, you get the snacks?”

“Deal.”


End file.
